Molecules | |
Enantio- and Periselective Nitroalkene Diels-Alder Reactions Catalyzed by Helical-Chiral Hydrogen Bond Donor Catalysts | |
Zhili Peng1  Maurice J. Narcis1  | |
[1] id="af1-molecules-18-09982">Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, FL 33146, U | |
关键词: asymmetric catalysis; nitroalkene; Diels-Alder reaction; helical chirality; | |
DOI : 10.3390/molecules18089982 | |
来源: mdpi | |
【 摘 要 】
Helical-chiral double hydrogen bond donor catalysts promote the nitroalkene Diels-Alder reaction in an enantio- and periselective manner. This represents the first asymmetric catalytic nitroalkene Diels-Alder reaction via LUMO-lowering catalysis. To gain an insight into this new process, the substrate scope of our catalyst was investigated by exploiting readily available 5-substituted pentamethylcyclopentadienes. The catalyst was found to tolerate dienes with different steric demands as well as dienes substituted with heteroatoms. The synthetic utility of 5-substituted pentamethylcyclopentadienes is rather limited, and thus we have developed a three-step route to 1,4,5,5-tetrasubstituted cyclopentadienes from commercially available ketones.
【 授权许可】
CC BY
© 2013 by the authors; licensee MDPI, Basel, Switzerland.
【 预 览 】
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